Planta Med 2015; 81 - SL4A_04
DOI: 10.1055/s-0035-1565334

Anti-inflammatory stilbenoids and cannabispiradienone derivatives from Tragopogon tommasinii Sch.Bip.

S Granica 1, 2, JP Piwowarski 1, A Randanzzo 4, P Schneider 2, B Żyżyńska-Granica 5, C Zidorn 2, 3
  • 1Department of Pharmacognosy and Molecular Basis of Phytoterapy, Medical University of Warsaw, Warszawa, Poland
  • 2Institute of Pharmacy, Department of Pharmacognosy, University of Innsbruck, Innsbruck, Austria
  • 3Istituto di Chimica Biomolecolare – Consiglio Nazionale delle Ricerche, Pozzuoli, Italy
  • 4Department of Pharmacy, University of Naples Federico II, Napoli, Italy
  • 5Department of Pharmacodynamics, Medical University of Warsaw, Warszawa, Poland

Tragopogon tommasinii Sch.Bip. is a perennial plant with large yellow flowering heads, endemic to the Illyrian floristic region. Previous phytochemical studies Tragopogon taxa yielded flavonoids, phenolic acids, sterols, triterpenes, triterpene glycosides, and triterpene saponins.

An extract prepared from aerial parts of T. tommassinii was fractionated using column chromatography with different media followed by the preparative HPLC to yield seven new natural products comprising three simple bibenzyls [2-carboxyl-5-hydroxy-3-methoxy-4'-β-glucopyranosyloxybibenzyl (1), 3-caffeoyl-(9-> 5)-β-apiosyl-(1-> 6)-β-glucopyranosyloxy-5,4'-dihydroxy-3'-methoxybibenzyl (2), 3-caffeoyl-(9-> 5)-β-apiosyl-(1-> 6)-β-glucopyranosyloxy-4'-dihydroxy-5,3'-dimethoxybibenzyl (3)], two phthalides [7-β-glucopyranosyloxy-(S)-3-(4-hydroxybenzyl)-5-methoxyphthalide (4), and 7-(1-> 6)-α-rhamnosyl-β-glucopyranosyloxy-(S)-3-(4-hydroxybenzyl)-5-methoxyphthalide (5)], and two cannabispiradienone derivatives [3-O-β-glucopyranosyldemethoxycannabispiradienone (6) and 3-caffeoyl-(9-> 5)-β-apiosyl-(1-> 6)-β-glucopyranosyloxydemethoxycannabispiradienone (7)] (Fig. 1). All compounds were tested as potential anti-inflammatory agents using the LPS-stimulated human neutrophils model. The influence of compounds at a concentration of 50 µM on the production of IL-8, IL-1β, TNF-α, and MMP-9 was investigated. Compounds 3, 5, and 7 had the strongest effect and were able to decrease IL-8, IL-1β, and TNF-α production by 27 – 62%, 7 – 29%, and 70 – 83%, respectively. Additionally, compounds 3 and 4 were able to lower the level of MMP-9 by 20 – 30%. Thus, the isolated compounds could be interesting lead structures for further bioactivity studies.

Acknowledgements: This work was supported by the Fonds zur Förderung der wissenschaftlichen Forschung (FWF, grant P201278-B16 to CZ), the Polish National Science Centre (DEC-2013/08/T/NZ7/00318, PhD fellowship to SG), and the Foundation for Polish Science (START to SG).